Claims
- 1. A process for preparing a zearalene type compound which comprises treating a zearalenone compound having the structural formula ##SPC5##
- wherein R is selected from the group consisting of hydrogen, lower alkyl, monocyclic aryl and lower alkanoyl, in a solvent selected from the group consisting of dioxane, ethyl acetate, ethyl ether, tetrahydrofurane, acetic anhydride and propionic anhydride, under keto-reducing conditions in the presence of keto-reducing amounts of zinc and hydrogen halide selected from the group consisting of hydrogen fluoride, hydrogen bromide, and hydrogen chloride, to convert the keto group of the zearalenane compound to a methylene group to obtain a zearalene compound having the structural formula ##SPC6##
- wherein R has the same meaning set forth above.
- 2. The process of claim 1 wherein the solvent is dioxane.
- 3. The process of claim 2 wherein R is hydrogen.
- 4. The process of claim 1 wherein the solvent is acetic anhydride.
- 5. The process of claim 4 wherein at least one R in the zearalenone compound is hydrogen and, during reduction, is converted to an acetyl group on the zearalene compound; the hydrogen halide is hydrogen chloride; and the reduction is conducted at a temperature from about -20.degree.C. to +50.degree.C.
- 6. The process of claim 5 wherein the zinc is employed in the solvent in an amount from about 1 to 20 parts by weight per part by weight of the zearalenone compound; the hydrogen halide is incorporated in the solvent in an amount from about 10 to 40 weight percent based on the weight of the solvent; and the solvent is employed in an amount from about 5 to 50 parts by weight per part by weight of the zearalenone compound.
- 7. The process of claim 6 wherein the zinc is employed in an amount from about 2.5 to 8 parts by weight per part by weight of the zearalenone compound.
- 8. The process of claim 7 wherein the reduction is conducted at a temperature from about -10.degree.C. to +20.degree.C.
- 9. The process of claim 5 wherein the zearalenone compound is 1'-trans-(10'S)-zearalenone; the zearalene compound resulting from the reduction is 2,4-diacetyl-1'-trans-(10'S)-zearalene which is subjected to hydrolysis conditions including an esterification agent in the presence of an esterification catalyst to produce zearalene.
- 10. The process of claim 9 wherein the esterification agent is a lower alkanol.
- 11. The process of claim 10 wherein the esterification catalyst is an alkali metal alkoxide.
- 12. The process of claim 11 wherein the catalyst is sodium methoxide.
- 13. The process of claim 10 wherein the esterification catalyst is an acid halide.
- 14. The process of claim 13 wherein the catalyst is hydrogen halide and the hydrolysis is conducted under reflux conditions.
Parent Case Info
This is a continuation of application Ser. No. 476,888, filed June 6, 1974, now abandoned.
Non-Patent Literature Citations (4)
Entry |
yamamura et al., J. Chem. Soc., pp. 2887-2889 (1968). |
Yamamura et al., Chemical Communications, pp. 1049-1050 (1967). |
Toda et al., Chemical Communications, pp. 919-920 (1969). |
Toda et al., Bulletion of the Chemical Society of Japan, Vol. 46, pp. 264-266 (1972). |
Continuations (1)
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Number |
Date |
Country |
Parent |
476888 |
Jun 1974 |
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